CA2341345C - Dissociation des racemates d'amides primaires catalysee par enzyme - Google Patents

Dissociation des racemates d'amides primaires catalysee par enzyme Download PDF

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Publication number
CA2341345C
CA2341345C CA2341345A CA2341345A CA2341345C CA 2341345 C CA2341345 C CA 2341345C CA 2341345 A CA2341345 A CA 2341345A CA 2341345 A CA2341345 A CA 2341345A CA 2341345 C CA2341345 C CA 2341345C
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CA
Canada
Prior art keywords
amine
ester
primary amine
optically active
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
CA2341345A
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English (en)
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CA2341345A1 (fr
Inventor
Christoph Nubling
Klaus Ditrich
Christian Dully
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BASF SE
Original Assignee
BASF SE
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Publication date
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Publication of CA2341345A1 publication Critical patent/CA2341345A1/fr
Application granted granted Critical
Publication of CA2341345C publication Critical patent/CA2341345C/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
    • C12P41/007—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Enzymes And Modification Thereof (AREA)

Abstract

La présente invention concerne un procédé de dissociation des racémates d'amines primaires à substitution alcoxy, par réaction avec un ester, en présence d'une lipase, cette réaction étant suivie de la séparation, de l'acide à l'origine de l'ester, de l'amine optiquement active ainsi formée, puis de la racémisation et du recyclage de l'énantiomère non souhaité de l'amine, ainsi que de l'estérification et du recyclage de l'acide.
CA2341345A 1998-08-20 1999-08-13 Dissociation des racemates d'amides primaires catalysee par enzyme Expired - Lifetime CA2341345C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19837745.2 1998-08-20
DE19837745A DE19837745A1 (de) 1998-08-20 1998-08-20 Enzymkatalysierte Racematspaltung von primären Aminen
PCT/EP1999/005958 WO2000011203A1 (fr) 1998-08-20 1999-08-13 Dissociation des racemates d'amides primaires catalysee par enzyme

Publications (2)

Publication Number Publication Date
CA2341345A1 CA2341345A1 (fr) 2000-03-02
CA2341345C true CA2341345C (fr) 2010-10-26

Family

ID=7878111

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2341345A Expired - Lifetime CA2341345C (fr) 1998-08-20 1999-08-13 Dissociation des racemates d'amides primaires catalysee par enzyme

Country Status (12)

Country Link
US (1) US6465223B1 (fr)
EP (1) EP1119634B1 (fr)
JP (1) JP4493851B2 (fr)
CN (1) CN1161477C (fr)
AT (1) ATE267874T1 (fr)
AU (1) AU5516499A (fr)
BR (1) BR9913101A (fr)
CA (1) CA2341345C (fr)
DE (2) DE19837745A1 (fr)
DK (1) DK1119634T3 (fr)
ES (1) ES2221423T3 (fr)
WO (1) WO2000011203A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19956786A1 (de) * 1999-11-25 2001-05-31 Basf Ag Verfahren zur Herstellung optisch aktiver Amine
AU2001294377A1 (en) * 2000-09-08 2002-03-22 Dsm N.V. Method for the preparation of enantiomerically enriched amines
US7951566B2 (en) * 2005-12-13 2011-05-31 E.I. Du Pont De Nemours And Company Production of peracids using an enzyme having perhydrolysis activity
DE102006032061B4 (de) * 2006-07-11 2009-01-02 Mark, Christoph, Dr. Verfahren zur Herstellung von optisch aktiven Aminen
ATE499448T1 (de) * 2006-09-13 2011-03-15 Basf Se Verfahren zur herstellung von optisch aktivem 2- benzyloxycyclohexylamin
WO2023160805A1 (fr) * 2022-02-25 2023-08-31 Symrise Ag Parfums à structure méthoxy-acétate
CN114561440B (zh) * 2022-04-27 2022-07-29 天津全和诚科技有限责任公司 一种高纯(r)-(+)-1-(4-甲氧基苯)乙胺单体的制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4332738A1 (de) * 1993-09-25 1995-03-30 Basf Ag Racematspaltung primärer und sekundärer Amine durch Enzym-katalysierte Acylierung
US6214608B1 (en) * 1995-02-03 2001-04-10 Basf Aktiengesellschaft Resolution of racemates of primary and secondary heteroatom-substitued amines by enzyme-catalyzed acylation
DE19637336A1 (de) * 1995-12-06 1997-06-12 Bayer Ag Verfahren zur Herstellung von optisch aktiven Aminen
DE19603575A1 (de) * 1996-02-01 1997-08-07 Bayer Ag Verfahren zur Herstellung von optisch aktiven Aminen
US5981267A (en) * 1996-01-24 1999-11-09 The Scripps Research Institute Enantioselection of amines using homocarbonates with hydrolase
DE19621686A1 (de) * 1996-05-30 1997-12-04 Bayer Ag Verfahren zur Herstellung von optisch aktiven Aminen
JP2001523969A (ja) * 1997-05-01 2001-11-27 ジー．ディー．サール アンド カンパニー キラルベータアミノ酸の製造方法および製造装置
DE19727517A1 (de) * 1997-06-30 1999-01-07 Basf Ag Racematspaltung von Aminosäureestern durch Enzym-katalysierte Acylierung

Also Published As

Publication number Publication date
DE19837745A1 (de) 2000-02-24
EP1119634B1 (fr) 2004-05-26
CN1161477C (zh) 2004-08-11
US6465223B1 (en) 2002-10-15
CA2341345A1 (fr) 2000-03-02
AU5516499A (en) 2000-03-14
ATE267874T1 (de) 2004-06-15
JP4493851B2 (ja) 2010-06-30
JP2002523055A (ja) 2002-07-30
CN1313905A (zh) 2001-09-19
WO2000011203A1 (fr) 2000-03-02
EP1119634A1 (fr) 2001-08-01
DE59909610D1 (de) 2004-07-01
DK1119634T3 (da) 2004-06-28
BR9913101A (pt) 2001-05-08
ES2221423T3 (es) 2004-12-16

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